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WO1990014366A1 - Perfluoropolymeres contenant un cyano et ayant des sites de polymerisation d'iode - Google Patents

Perfluoropolymeres contenant un cyano et ayant des sites de polymerisation d'iode Download PDF

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Publication number
WO1990014366A1
WO1990014366A1 PCT/US1990/002602 US9002602W WO9014366A1 WO 1990014366 A1 WO1990014366 A1 WO 1990014366A1 US 9002602 W US9002602 W US 9002602W WO 9014366 A1 WO9014366 A1 WO 9014366A1
Authority
WO
WIPO (PCT)
Prior art keywords
perfluoropolymer
perfluoro
ether
alkyl vinyl
cyano
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1990/002602
Other languages
English (en)
Inventor
Anestis Leonidas Logothetis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to DE69013915T priority Critical patent/DE69013915T2/de
Priority to EP90907553A priority patent/EP0475959B1/fr
Publication of WO1990014366A1 publication Critical patent/WO1990014366A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/26—Tetrafluoroethene
    • C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers

Definitions

  • fluoropolymer that has been used in elastomeric applications is that prepared from tetrafluoroethylene (TFE) and perfluoro (alkyl vinyl) ether, and particularly perfluro (methyl vinyl) ether (PMVE).
  • TFE tetrafluoroethylene
  • PMVE perfluoro (methyl vinyl) ether
  • a small percentage of termonomer is generally incorporated, such as the cyano- or
  • the perfluoropolymers previously made from TFE, PMVE and a cure site monomer typically exhibit a high concentration of ionic end groups, such as carboxylic or sulfonic acid moieties, which are introducted from the initiating system.
  • Conventional chain transfer agents can be used to lower the ionic end groups, such as carboxylic or sulfonic acid moieties, which are introducted from the initiating system.
  • Conventional chain transfer agents can be used to lower the
  • the instant invention relates to improved perfluoropolymer compositions which, when compounded and cured as elastomers, exhibit an excellent
  • the present invention provides, in a perfluoropolymer having randomly copolymerized units of tetrafluoroethylene, perfluro (alkyl vinyl) ether and fluorinated curesite monomer containing nitrile groups, the improvement wherein the
  • perfluoropolymer further comprises iodo moieties present in an amount of least about 0.05 percent, by weight of the perfluoropolymer.
  • Patent 3,132,123 which is hereby incorporated by reference.
  • perfluoro (alkyl vinyl) ethers perfluoro (methyl vinyl) ether (PMVE) has been found to be particularly satisfactory.
  • Other perfluoro (alkyl vinyl) ethers which can be used in the present
  • perfluoro (alkoxy alkyl vinyl) ethers such as those described in Fritz et al., U.S. Patent 3,291,843, also hereby incorporated by
  • perfluoro alkoxy alkyl vinyl
  • perfluoro (5-methyl-3,6-dioxa-l-nonene) has been found to be particularly satisfactory.
  • cyano- cure sites can be incorporated into these polymers, including those described in Breazeale, U.S. Patent 4,281,092, hereby incorporated by reference.
  • the polymers of this invention preferably contain such curesites randomly distributed along the backbone of the perfluoropolymer.
  • a central aspect of the present invention is that the perfluoropolymer comprise iodine moieties.
  • the iodo moieties in the present compositions can be incorporated by conducting the radical copolymerization of the basic monomers noted above in the presence of an iodine-containing compound represented by the formula RI X , where R is a hydrocarbon or saturated fluorocarbon or chlorofluorocarbon residue having 1 to 8 carbon atoms and x is an integer of 1 or 2 , corresponding to the valence of the residue R.
  • R is a hydrocarbon or saturated fluorocarbon or chlorofluorocarbon residue having 1 to 8 carbon atoms and x is an integer of 1 or 2 , corresponding to the valence of the residue R.
  • the iodo compound acts as a chain transfer agent, resulting in a telomerization
  • the fluoropolymer chain may therefore have iodine groups at each end, and the telomerization polymerization process will occur at each end of the polymer chain.
  • Iodocompounds which can be used in the preparation of the perfluoropolymer of the present invention include, for example, those based on
  • hydrocarbon residue such as methylene iodide
  • 1,4-diiodo butane, and butyl iodide and those based on saturated fluorocarbon or chlorofluorocarbon residue such as monoiodo perfluoromethane, diiodo methane, monoiodo perfluoroethane, monoiodo perfluoro propane, monoiodopropane, 1,3-diiodoperfluoro-n-propane, 1,4- diiodo-n-butane, 1,4-diiodoperfluoro-n-butane,
  • the amount of iodo-compound used should be high enough to give extensive chain transfer and result in incorporation of at least about 0.05 weight % of iodine in the perfluoropolymer. High chain transfer efficiency by the alkyl iodide results in a
  • perfluoropolymer with lower compound viscosity and a relatively narrow molecular weight distribution with a typical value of Mw/Mn of about 2-3, for desirable rheology and processing characteristics.
  • the concentration of iodine in the polymer should be about from 0.05 to 1.0 weight %, and preferably 0.1-0.5 weight %, based on the
  • the concentration in the fluoropolymer will depend upon the concentration of alkyl iodides in the polymerization medium and upon polymerization conditions, which will effect the chain transfer efficiency.
  • the upper limit on iodine content corresponds approximately to the practical lower limit on polymer viscosity, since higher concentrations of iodine gives polymers with lower molecular weight and viscosity.
  • the iodine concentration in the fluoropolymer will depend upon the concentration of alkyl iodides in the polymerization medium and upon polymerization conditions, which will effect the chain transfer efficiency.
  • the upper limit on iodine content corresponds approximately to the practical lower limit on polymer viscosity, since higher concentrations of iodine gives polymers with lower molecular weight and viscosity.
  • perfluoropolymer can be determined by conventional analytical techniques, such as elemental analysis.
  • the lower limit of iodine incorporation is approximately that at which a significant effect on the cure rate and vulcanizate properties is found when cured by peroxides.
  • the upper limit on iodine content corresponds approximately to the practical lower limit on polymer viscosity, since higher concentrations of iodine gives polymers with lower molecular weight and viscosity.
  • the upper limit on iodine content also relates to the desired highest state of cure, insofar as it relates to the efficiency of formation of chains terminated with iodo groups.
  • the components of the perfluoropolymers are present in the amounts generally used in the following
  • Patent 4,281,092 Concentrations of about from 0.1 to 5.0 weight % of the cyano- moiety have been found to provide particularly good processing characteristics.
  • the perfluoropolymers of the present invention can be made by free radical emulsion
  • polymerization temperatures can be in the range of about from 40 to 130°C, and preferably about from 70 to 115°C, at pressures of about from 2 to 8 MPa and residence time
  • Free radical generation is effected using a water-soluble initiator such as ammonium persulfate, either by thermal decomposition or by reaction with a reducing agent such as sodium sulfite.
  • a water-soluble initiator such as ammonium persulfate
  • a reducing agent such as sodium sulfite.
  • the alkyl iodides can be fed into the reactor directly or as a solution. Initiator levels are set low enough so that iodine end groups predominate over those from initiator fragments. This leads to the desired low polymer viscosity and high solubility.
  • the polymer dispersion is stabilized with an inert surface-active agent such as ammonium perfluorooctanoate, usually with addition of a base such as sodium hydroxide or a buffer such as disodium phosphate to control pH in the range 3 to 7.
  • an inert surface-active agent such as ammonium perfluorooctanoate
  • a base such as sodium hydroxide or a buffer such as disodium phosphate
  • unreacted monomer is removed from the reactor effluent latex by vaporization at reduced pressure.
  • Polymer can be recovered from latex by coagulation, e.g., by reducing pH to about 3 by acid addition and adding a salt solution such as calcium nitrate, magnesium sulfate, or potassium aluminum sulfate in water, followed by separation of serum from polymer, washing with water, and drying of the wet polymer.
  • the iodine concentration in the perfluoropolymer can be determined by conventional analytical techniques, such
  • Perfluoropolymers of the present invention are typically compounded with one or more of the additives known to be useful in perfluoropolymer compositions, such as pigments, fillers, pore-forming agents and plasticizers. It is particularly,
  • a curable composition comprises polymer and a peroxide to generate free radicals at curing temperatures.
  • a dialkyl peroxide which
  • di-tertiarybutyl peroxide having a tertiary carbon atom attached to peroxy oxygen may be particularly
  • peroxides of this type are 2,5- dimethyl-2,5-di(tertiarybutylperoxy) hexyne-3 and 2,5- dimethyl-2,5-di (tertiarybutylperoxy) hexane.
  • Other peroxides can be selected from such compounds as dicumyl peroxide, dibenzoyl peroxide, tertiarybutyl perbenzoate, and di[1,3-dimethyl-3-(t-butylperoxy) butyl]carbonate, and the like.
  • the resulting perfluoroelastomers exhibit particularly good processing characteristics, including curing and mold release properties.
  • Perfluoroelastomers of TFE, PMVE and cure site monomer have typically been difficult to process in milling, extrusion and molding operations, because of their high bulk viscosities. While the superior performance of the present compositions is not fully understood, it is believed that the selection of iodo compounds, which function as chain transfer agents, results in iodo end groups for the polymer chains, and these end groups are reactive to crosslinking agents. When used in
  • the iodides permit the curing of relatively low molecular weight polymers with peroxides to give parts with very good properties.
  • the polymers can be cured with greater ease and with high yields.
  • complicated parts which could not be made with
  • the perfluoropolymers of the present invention react with peroxide curing agents and
  • crosslinking coagents to give unique polymer networks in which crosslinks are formed both at random points along the polymer chain and at the ends of the chains.
  • Such polymers have excellent strength and compression set properties, as well as good processing
  • the perfluoropolymers per se can also be used in a wide variety of applications.
  • the present compositions have been found to be particularly useful as antireflective coatings for pellicles, for example, in the protection of printed circuits.
  • a coating of perfluoroelastomers of the present invention of about from 0.2 to 1.0 microns, on a substrate of nitrocellulose, provides a pellicle material having an outstanding combination of adhesion to both the
  • perfluoroelastomer was prepared from TFE, PMVE, and perfluoro-(8-cyano-5-methyl-3,6-dioxa-1-octene)
  • the polymers were prepared in a 1 liter mechanically agitated, waterjacketed, stainless-steel autoclave operated continuously at 90°C and 4800 KPa into which was pumped, at a rate of 250 ml/hr an aqueous polymerization medium/initiator solution comprising of 8 liters of water, 32 g. ammonium
  • perfluoro(methyl vinyl) ether 85 g/hr was also fed simultaneously to the autoclave at a consant rate by means of a diaphragm compressor.
  • Polymer latex was removed by means of a let-down valve and unreacted monomers were vented.
  • the latex from 14 hrs operations was added with stirring to a preheated (95°C) coagulating solution consisting of 1840 g MgSO 4 .7H 2 O in 40 liters of water.
  • the dried polymer weighed 1825 gs. and had the composition, as weight % of the polymer, of tetrafluoroethylene 55.6, perfluoro(methyl vinyl) ether 42.6, 8CNVE 1.4 and iodine 0.32. The inherent viscosity of the polymer was determined at
  • perfluoroelastomers were prepared with hydrocarbon alkyl iodides (RI or IRI), which provided iodo moieties on the ends of some of the polymer chains.
  • RI or IRI hydrocarbon alkyl iodides
  • the 8CNVE cure sites in these polymers were randomly dispersed in the backbone.
  • the methylene iodide was dissolved in t-butanol as a 10% solution because it was not soluble in F113.
  • the compounding and curing were identical to the conditions used in Examples 1-5, and the results are shown in Table 2.
  • the iodo-containing polymers exhibit faster cure rates when compared to Control Example B as well as improved vulcanizate properties.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

Des perfluoropolymères sont préparés à partir de tétrafluoroéthylène, perfluoro (alkyle vinyle) éther et d'un monomère à site de polymérisation cyano, et comprennent en outre des fractions iodo; des élastomères polymérisées sont préparés à partir de ces perfluoropolymères.
PCT/US1990/002602 1989-05-19 1990-05-14 Perfluoropolymeres contenant un cyano et ayant des sites de polymerisation d'iode Ceased WO1990014366A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE69013915T DE69013915T2 (de) 1989-05-19 1990-05-14 Cyanidhaltige perfluorpolymere mit iodatomen als vernetzungsstellen.
EP90907553A EP0475959B1 (fr) 1989-05-19 1990-05-14 Perfluoropolymeres contenant un groupement cyano et ayant des sites de reticulation iode

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US354,193 1989-05-19
US07/354,193 US4972038A (en) 1989-05-19 1989-05-19 Cyano-containing perfluoropolymers having iodine curesites

Publications (1)

Publication Number Publication Date
WO1990014366A1 true WO1990014366A1 (fr) 1990-11-29

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US (1) US4972038A (fr)
EP (1) EP0475959B1 (fr)
JP (1) JP2888971B2 (fr)
DE (1) DE69013915T2 (fr)
WO (1) WO1990014366A1 (fr)

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US4612357A (en) * 1985-07-09 1986-09-16 E. I. Du Pont De Nemours And Company Melt-processible tetrafluoroethylene copolymers and process for preparing them
EP0208314A2 (fr) * 1985-07-12 1987-01-14 E.I. Du Pont De Nemours And Company Elastomères fluorés

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DE69013915D1 (de) 1994-12-08
JP2888971B2 (ja) 1999-05-10
EP0475959B1 (fr) 1994-11-02
US4972038A (en) 1990-11-20
EP0475959A1 (fr) 1992-03-25
EP0475959A4 (en) 1992-05-06
DE69013915T2 (de) 1995-03-09
JPH05500070A (ja) 1993-01-14

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